Details
Stereochemistry | RACEMIC |
Molecular Formula | C11H17NO |
Molecular Weight | 179.2588 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CNC(C)CC1=CC=C(OC)C=C1
InChI
InChIKey=UGFMBZYKVQSQFX-UHFFFAOYSA-N
InChI=1S/C11H17NO/c1-9(12-2)8-10-4-6-11(13-3)7-5-10/h4-7,9,12H,8H2,1-3H3
Molecular Formula | C11H17NO |
Molecular Weight | 179.2588 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/26930544Curator's Comment: The description was created based on several sources, including
http://www.who.int/medicines/access/controlled-substances/5.6_PMMA_CRev.pdf | https://www.ncbi.nlm.nih.gov/pubmed/28506818
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26930544
Curator's Comment: The description was created based on several sources, including
http://www.who.int/medicines/access/controlled-substances/5.6_PMMA_CRev.pdf | https://www.ncbi.nlm.nih.gov/pubmed/28506818
4-Methoxymethamphetamine (PMMA, para-Methoxymethamphetamine) is a stimulant and psychedelic drug closely related to the amphetamine-class serotonergic drug para-methoxyamphetamine (PMA). Little is known about the pharmacological properties, metabolism, and toxicity of 4-Methoxymethamphetamine. Because of its structural similarity to para-methoxyamphetamine, which has known toxicity in humans, it is thought to have considerable potential to cause harmful side effects or death in overdose. In the early 2010s, a number of deaths in users of the drug MDMA were linked to misrepresented tablets and capsules of 4-Methoxymethamphetamine. In 2010–2013, a cluster of 29 fatal poisonings related to the toxic designer drug 4-Methoxymethamphetamine was revealed in Norway. The toxicity of PMMA is regarded as substantially higher than for amphetamine, methamphetamine, and MDMA, as indicated by 131 fatal and 31 nonfatal poisonings associated with the abuse of 4-Methoxymethamphetamine worldwide. The toxicity of 4-Methoxymethamphetamine is positively correlated with the 4-Methoxymethamphetamine dose and the blood drug level, but the existing literature indicates that certain human subjects may have an increased risk of 4-Methoxymethamphetamine toxicity. 4-Methoxymethamphetamine, like PMA most likely acts as a selective serotonin releasing agent (SSRA) with weak effects on dopamine and norepinephrine transporters. However, relative to MDMA, it is considerably less effective as a serotonin releaser with properties more akin to a reuptake inhibitor in comparison. It evokes robust hyperthermia while producing only modest hyperactivity and serotonergic neurotoxicity, substantially lower than that caused by MDMA.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL238 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28506818 |
83.0 µM [IC50] | ||
Target ID: CHEMBL222 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28506818 |
7.4 µM [IC50] | ||
Target ID: CHEMBL228 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28506818 |
180.0 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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PubMed
Title | Date | PubMed |
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Evaluation of the neurotoxicity of N-methyl-1-(4-methoxyphenyl)-2-aminopropane (para-methoxymethamphetamine, PMMA). | 1992 Sep 4 |
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A re-examination of the mono-methoxy positional ring isomers of amphetamine, methamphetamine and phenyl-2-propanone. | 2001 Jun 15 |
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Identification and synthesis of some contaminants present in 4-methoxyamphetamine (PMA) prepared by the Leuckart method. | 2002 Jun 25 |
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New designer drug p-methoxymethamphetamine: studies on its metabolism and toxicological detection in urine using gas chromatography-mass spectrometry. | 2003 Jun 5 |
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Identification of human cytochrome P450 2D6 as major enzyme involved in the O-demethylation of the designer drug p-methoxymethamphetamine. | 2004 Apr |
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Analgesic and behavioral effects of amphetamine enantiomers, p-methoxyamphetamine and n-alkyl-p-methoxyamphetamine derivatives. | 2004 Oct |
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Determination of a newly encountered designer drug "p-methoxyethylamphetamine" and its metabolites in human urine and blood. | 2008 May 2 |
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Studies on distribution of para-methoxymethamphetamine (PMMA) designer drug in rats using gas chromatography-mass spectrometry. | 2009 Apr |
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[Cases of fatal para methoxy amphetamine (PMA) poisoning in the material of the Forensic Medicine Department, Medical University Of Białystok, Poland]. | 2009 Jul-Sep |
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Studies on distribution and metabolism of para-methoxymethamphetamine (PMMA) in rats after subcutaneous administration. | 2009 May 2 |
Patents
Sample Use Guides
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28506818
Human embryonic kidney (HEK) 293 cells stably expressing human DAT, NET or SERT were used for activity evaluation. Uptake activity of hNET, hDAT and hSERT was measured using the
Neurotransmitter Transporter Uptake Assay Kit from MDS Analytical Technologies (Sunnyvale, CA). On day 0, HEK 293 cells were seeded at a density of approximately 60.000 cells/well in clear-bottom, black-walled, 96-well plates (Greiner Bio-one, Solingen Germany) coated with PLL buffer (50 mg/L). Cells were allowed to proliferate overnight in a humidified 5% CO2/95% air
atmosphere at 37 °C. Experiments were performed the next day (day 1). Cells were pre-incubated with the fluorescent substrate for 12 min prior to a 30 min drug exposure. Culture medium was replaced by 100 μL/well fluorescent substrate solution, and uptake measurements were started. At t= 0, 100 μL/well HBSS without (control) or with drug was added to each well and uptake was measured continuously for 30 min. Background wells were pre-incubated with 100 μL/well HBSS without fluorescent substrate solution and exposed at t =0 min to 100 μL/well HBSS without drugs. Non-transfected HEK 293 cells pre-incubated with 100 μL/well fluorescent substrate solution and exposed at t= 0 to 100 μL/well HBSS without drugs served as negative controls. Drugs were prepared daily in HBSS from 2 or 100 mM stock solutions. Cocaine, DL-amphetamine, MDMA, 4-FA, MXE, PMMA, 2C-B, 25B-NBOMe, 25I-NBOMe, α-PVP and 5-APB were measured at final concentrations of 0.01–1000 μM.
Substance Class |
Chemical
Created
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Record UNII |
037U5SR9KL
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Record Status |
Validated (UNII)
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PiHKAL
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WIKIPEDIA |
Designer-drugs-4-Methoxymethamphetamine
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DEA NO. |
1245
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88543-18-4
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100000183097
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PARA-METHOXY-N-METHYLAMPHETAMINE
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admin on Sat Dec 16 11:01:29 GMT 2023 , Edited by admin on Sat Dec 16 11:01:29 GMT 2023
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PRIMARY | para-Methoxy-N-methylamphetamine (also known as PMMA, Red Mitsubishi), chemically known as methyl-MA, 4-methoxy-N-methylamphetamine, or 4-MMA) is a stimulant and psychedelic drug closely related to the amphetamine-class serotonergic drug para-methoxyamphetamine (PMA). PMMA is the 4-methoxy analog of methamphetamine. Little is known about the pharmacological properties, metabolism, and toxicity of PMMA; because of its structural similarity to PMA, which has known toxicity in humans, it is thought to have considerable potential to cause harmful side effects or death in overdose. In the early 2010s, a number of deaths in users of the drug MDMA were linked to misrepresented tablets and capsules of PMMA. | ||
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90766
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